Asymmetric synthesis of β′-amino-α,β-enones via addition of α,β-unsaturated ketone-derived enolates to chiral N-phosphonyl imines

Yiwen Xiong; Haibo Mei; Jianlin Han; Guigen Li; Yi Pan

doi:10.1016/j.tetlet.2014.03.005

Asymmetric synthesis of β′-amino-α,β-enones via addition of α,β-unsaturated ketone-derived enolates to chiral N-phosphonyl imines

Yiwen Xiong, Haibo Mei, Jianlin Han, Guigen Li, Yi Pan

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

3 Scopus citations

Abstract

Efficient asymmetric Mannich addition reactions between α,β-unsaturated ketone derived enolates and N-phosphonyl imines were reported. These reactions could proceed smoothly for a variety of imine substrates with good (up to 96%) chemical yields and excellent diastereoselectivities (up to 98:2 dr). The method reported in this work provides an easy access to chiral β′-amino-α,β-enones.

Original language	English
Pages (from-to)	2476-2479
Number of pages	4
Journal	Tetrahedron Letters
Volume	55
Issue number	15
DOIs	https://doi.org/10.1016/j.tetlet.2014.03.005
State	Published - Apr 9 2014

Keywords

Asymmetric Mannich reaction
Diastereoselectivity
N-Phosphonyl imine
α,β-Unsaturated ketone
β′-Amino-α,β-enones

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10.1016/j.tetlet.2014.03.005

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title = "Asymmetric synthesis of β′-amino-α,β-enones via addition of α,β-unsaturated ketone-derived enolates to chiral N-phosphonyl imines",

abstract = "Efficient asymmetric Mannich addition reactions between α,β-unsaturated ketone derived enolates and N-phosphonyl imines were reported. These reactions could proceed smoothly for a variety of imine substrates with good (up to 96%) chemical yields and excellent diastereoselectivities (up to 98:2 dr). The method reported in this work provides an easy access to chiral β′-amino-α,β-enones.",

keywords = "Asymmetric Mannich reaction, Diastereoselectivity, N-Phosphonyl imine, α,β-Unsaturated ketone, β′-Amino-α,β-enones",

author = "Yiwen Xiong and Haibo Mei and Jianlin Han and Guigen Li and Yi Pan",

year = "2014",

month = apr,

day = "9",

doi = "10.1016/j.tetlet.2014.03.005",

language = "English",

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journal = "Tetrahedron Letters",

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TY - JOUR

T1 - Asymmetric synthesis of β′-amino-α,β-enones via addition of α,β-unsaturated ketone-derived enolates to chiral N-phosphonyl imines

AU - Xiong, Yiwen

AU - Mei, Haibo

AU - Han, Jianlin

AU - Li, Guigen

AU - Pan, Yi

PY - 2014/4/9

Y1 - 2014/4/9

N2 - Efficient asymmetric Mannich addition reactions between α,β-unsaturated ketone derived enolates and N-phosphonyl imines were reported. These reactions could proceed smoothly for a variety of imine substrates with good (up to 96%) chemical yields and excellent diastereoselectivities (up to 98:2 dr). The method reported in this work provides an easy access to chiral β′-amino-α,β-enones.

AB - Efficient asymmetric Mannich addition reactions between α,β-unsaturated ketone derived enolates and N-phosphonyl imines were reported. These reactions could proceed smoothly for a variety of imine substrates with good (up to 96%) chemical yields and excellent diastereoselectivities (up to 98:2 dr). The method reported in this work provides an easy access to chiral β′-amino-α,β-enones.

KW - Asymmetric Mannich reaction

KW - Diastereoselectivity

KW - N-Phosphonyl imine

KW - α,β-Unsaturated ketone

KW - β′-Amino-α,β-enones

UR - http://www.scopus.com/inward/record.url?scp=84897990788&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2014.03.005

DO - 10.1016/j.tetlet.2014.03.005

M3 - Article

AN - SCOPUS:84897990788

VL - 55

SP - 2476

EP - 2479

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 15

ER -